A Tutorial on Selectivity Determination in C(sp2)–H Oxidative Addition of Arenes by Transition Metal Complexes | Zendy

Tyler P. Pabst | Zendy; Paul J. Chirik | Zendy

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A Tutorial on Selectivity Determination in C(sp²)–H Oxidative Addition of Arenes by Transition Metal Complexes

Author(s) -

Tyler P. Pabst,

Paul J. Chirik

Publication year - 2021

Publication title -

organometallics

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.231

H-Index - 172

eISSN - 1520-6041

pISSN - 0276-7333

DOI - 10.1021/acs.organomet.1c00030

Subject(s) - chemistry , chemoselectivity , oxidative addition , regioselectivity , selectivity , oxidative phosphorylation , transition metal , aryl , transition state , chelation , halide , reductive elimination , medicinal chemistry , computational chemistry , photochemistry , stereochemistry , organic chemistry , alkyl , catalysis , biochemistry

A Tutorial on factors that determine the selectivity in C(sp 2 )-H activation and functionalization reactions involving two-electron oxidative addition processes with transition metals is presented. The interplay of the thermodynamics of C(sp 2 )-H oxidative addition and kinetic influences upon regioselectivity are presented alongside pedagogically valuable experimental and computational results from the literature. Mechanisms and energetics of chelate-assisted C(sp 2 )-H oxidative addition are examined, as are concepts related to chemoselectivity in the oxidative addition of C(sp 2 )-H or C(sp 2 )-X (X = F, Cl, Br, I) bonds with aryl halide substrates.

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